Shelter Island, NY Homes

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  $1,085,000

  • 3 Beds
  • 2 Baths

  26 Ole Buck Run, Shelter Island, NY 11964

  This recently renovated 3 bedroom, two bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors, painted interior, new back decks, exterior basement entry and new appliances. Turn key and ready for you to enjoy for Summer 2025.

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  26 Ole Buck Run, Shelter Island, NY 11964
• Explore Shelter Island

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  /21

  $18,000 per month

  • 5 Beds
  • 2 Baths
  • House for Rent

  6 Summerfield Place, Shelter Island, NY 11964

  Charming Summer Victorian on Water. The peaceful living room and dining room are surrounded by the stunning waterfront porch The open and comfortable eat-in-kitchen and family room are comfortable essentials to this easy living home. First floor bedroom with full bath along with five craftsman's bedrooms and waterfront screened in porch on the second floor completes this charmer! Near

  6 Summerfield Place, Shelter Island, NY 11964
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  $975,000 Sold May 20, 2025

  1 Rebel Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1981

  Last Sold Summary

  • 20% Below List Price
  • $662/SF
  • 174 Days On Market

  Current Estimated Value $1,522,000

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  1 Rebel Rd, Shelter Island, NY 11964
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  Est $1,894,000 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,628 Sq Ft

  45 New York Ave, Shelter Island, NY 11964

  45 New York Ave, Shelter Island, NY 11964
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  $1,375,000

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  20 Crescent Way, Shelter Island, NY 11964

  This lovely home is nicely sited ona shy acre close to Menhaden LaneBeach and Golf. Hard wood floors throughout.Spaciousliving room with cathedral ceiling, fireplace andsliders which open onto a large deck and yard beyond. Three nice sized bedrooms, two full baths, formal dining room, chef's kitchen with gas stove, Den/potential media roomwith egress, two-car garage+.Yard is fenced with plenty of

  Melina Wein M WEIN REALTY INC

  20 Crescent Way, Shelter Island, NY 11964
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  /26

  $14,400 per month

  • 4 Beds
  • 2 Baths
  • 2,669 Sq Ft
  • Property for Rent

  12 Dogwood Ln, Shelter Island, NY 11964

  Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  12 Dogwood Ln, Shelter Island, NY 11964
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  $3,500,000 Sold Feb 11, 2025

  44 Saint Mary's Rd, Shelter Island, NY 11964

  • 3 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $1,085/SF
  • 28 Days On Market

  Current Estimated Value $2,810,220

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate

  44 Saint Mary's Rd, Shelter Island, NY 11964
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  Est $1,625,119 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft

  16 Great Circle Dr, Shelter Island, NY 11964

  16 Great Circle Dr, Shelter Island, NY 11964
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  $4,250,000

  • 4 Beds
  • 5 Baths
  • 3,676 Sq Ft

  8 Cove Way, Shelter Island, NY 11964

  Enviably located on Shelter Island's southern coast with 113' of waterfront on Menantic Creek, this half-acre property was fully reimagined in a high-end 2017 renovation that left no detail overlooked. Offering 3,676 +/- sq. ft. across 2 levels, the home includes 4 bedrooms, 5 baths, 2 fireplaces, a heated gunite pool, outdoor kitchen, firepit, specimen gardens, and a private deep-water dock. A

  Stacey Cohen Saunders & Associates

  8 Cove Way, Shelter Island, NY 11964
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  /28

  $55,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  12 Cove Way, Shelter Island, NY 11964

  This house is the summer retreat you have been looking for. Centrally located down a private lane you will enjoy extraordinary views of the creek from the poolside patio. Private dock on this waterfront property for all the summer activities, just feet from the back door. This home offers a large chefs kitchen open to the living, dining and reading nook. Windows galore inviting the natural light.

  12 Cove Way, Shelter Island, NY 11964
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  $1,950,000 Sold Mar 14, 2025

  3 Sea Gull Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • Built 1953

  Last Sold Summary

  • 1% Below List Price
  • $1,182/SF
  • 322 Days On Market

  Current Estimated Value $2,369,670

  Last Listing Agent Cynthia Barrett Brown Harris Stevens Hamptons

  3 Sea Gull Rd, Shelter Island, NY 11964
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  Est $1,996,000 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  6 Behringer Ln, Shelter Island, NY 11964

  6 Behringer Ln, Shelter Island, NY 11964
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  /22

  $3,175,000

  • 3 Beds
  • 2 Baths
  • 1,373 Sq Ft

  13 Tarkettle Rd, Shelter Island, NY 11964

  Nestled on over an acre along Shelter Island's coveted Dickerson Creek, this Scandinavian-style waterfront cottage offers a serene escape with 100 ft. of gorgeous shoreline. Imagine waking up to breathtaking sunrises and launching your paddle board right from your backyard. Inside, discover a light-filled comfortable floor plan enhanced by Swedish-inspired decor. The home features three bedrooms

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  13 Tarkettle Rd, Shelter Island, NY 11964
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  $7,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,825 Sq Ft
  • House for Rent

  42 N Menantic Rd, Shelter Island, NY 11964

  Escape to Tranquility Base, a light-filled modern retreat where timeless mid-century style meets today’s elevated comforts. Thoughtfully renovated and expanded, this 4-bedroom, 2.5-bath home is surrounded by lush, landscaped grounds and designed for seamless indoor–outdoor living—thanks to five sliding glass doors that open to a heated gunite pool and expansive entertaining deck.Enjoy the

  Jeanmarie Bay William Raveis New York LLC

  42 N Menantic Rd, Shelter Island, NY 11964
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  $795,000 Sold Oct 10, 2025

  33B S Midway Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • Built 1950

  Last Sold Summary

  • 11% Below List Price
  • 142 Days On Market

  Last Listing Agent Shane Donahue The Agency Hamptons

  33B S Midway Rd, Shelter Island, NY 11964
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  Est $2,123,298 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  Unlisted Address

  Unlisted Address
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  $1,300,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  1 Meadow Place, Shelter Island, NY 11964

  Nestled off the road for added privacy this updated home offers Chase Creek water views. Featuring 2 bedrooms and 2 renovated bathrooms, the layout includes an office perfect for remote work or creative pursuits. The open-concept living and dining area is bright and inviting, flowing into the renovated kitchen with modern finishes and storage. Step out onto the back deck thru sliders from the

  Melina Wein M WEIN REALTY INC

  1 Meadow Place, Shelter Island, NY 11964
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  /20

  $38,500 per month

  • 3 Beds
  • 1 Bath
  • House for Rent

  91 Shore Rd, Shelter Island, NY 11964

  A romantic and secluded summer getaway. Enjoy a front row seat to breathtaking and dramatic views of the Shelter Island Sound, Crescent (Sunset) Beach, Quinipet Sailing, North Ferry, Greenport, Southold and 4th of July fireworks. Conveniently just steps from Kissing Rock, Crescent Beach, The Pridwin Hotel (Spa and Restaurant), Sunset Beach (Restaurant and Nightlife), Shelter Island House

  91 Shore Rd, Shelter Island, NY 11964
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  $2,650,000 Sold Oct 16, 2025

  7 Gazon Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $1,394/SF
  • 130 Days On Market

  Last Listing Agent Terry Thompson Douglas Elliman Real Estate

  7 Gazon Rd, Shelter Island, NY 11964
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  Est $1,086,115 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft

  105 S Ferry Rd, Shelter Island, NY 11964

  105 S Ferry Rd, Shelter Island, NY 11964
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  $1,095,000

  • Land
  • 0.64 Acre
  • $1,710,938 per Acre

  12 Hilo Dr, Shelter Island, NY 11964

  .64 Acres on Shelter Island, adjacent to cumminty dock. Room fof house and pool

  Brian Buckhout Compass

  12 Hilo Dr, Shelter Island, NY 11964
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  /18

  $63,000 per month

  • 3 Beds
  • 2 Baths
  • 1,487 Sq Ft
  • House for Rent

  4 Ivy Place, Shelter Island, NY 11964

  Located in Hay Beach, this year round furnished rental is available and fully furnished. 3 bedrooms and 2 full baths is located in the beautiful area of Hay Beach, just 2 minutes from Gardiners Bay Country Club. Large living room with fireplace and sliders out to the large awning covered deck. Large loft area off the living room could serve as an office area of for overflow guests.

  Sheri Winter Parker Corcoran

  4 Ivy Place, Shelter Island, NY 11964
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  $1,450,000 Sold May 30, 2025

  5 Wade Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Below List Price
  • $782/SF
  • 20 Days On Market

  Current Estimated Value $1,538,168

  Last Listing Agent Rosanna Piazza Signature Premier Properties

  5 Wade Rd, Shelter Island, NY 11964
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  Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft

  8 Crescent Way, Shelter Island, NY 11964

  8 Crescent Way, Shelter Island, NY 11964
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  /39

  $2,750,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,420 Sq Ft

  156 Ram Island Dr, Shelter Island, NY 11964

  Surrounded by preserved land this classic home has an absolutely magnificent setting that includes stunning water views. The open kitchen, breakfast room and family room creates a comfortable bright living area that walks out to a lovely patio overlooking Gardiners Bay . The more formal dining and living room with fireplace also provides amazing views of the water. The spacious primary bedroom

  Mary Elizabeth Galle Corcoran

  156 Ram Island Dr, Shelter Island, NY 11964
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  /20

  $65,000 per month

  • 4 Beds
  • 5 Baths
  • House for Rent

  9 Willow Pond Rd, Shelter Island, NY 11964

  This stunning home is only going to be offered one time as a summer vacation rental. Situated thoughtfully on the property to catch indirect natural light through-out the day this open, airy and bright home was custom built working side by side with owners and architect until perfection was reached. Enter this architectural delight through large glass doors off a stone front porch to be greeted

  9 Willow Pond Rd, Shelter Island, NY 11964
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  $4,350,000 Sold Oct 31, 2025

  7 Westmoreland Dr, Shelter Island, NY 11964

  • 6 Beds
  • 4.5 Baths
  • 4,957 Sq Ft
  • Built 1901

  Last Sold Summary

  • 1% Above List Price
  • $878/SF
  • 18 Days On Market

  Last Listing Agent Carl Gambino Compass Greater NY LLC

  7 Westmoreland Dr, Shelter Island, NY 11964
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  Est $1,443,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  79A N Midway Rd, Shelter Island, NY 11964

  79A N Midway Rd, Shelter Island, NY 11964
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  /36

  $3,750,000

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  52 S Midway Rd, Shelter Island, NY 11964

  Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical sunsets. Wide waterfront vistas unfold across beautiful landscaping by Marders, broad greens lined

  Shane Donahue The Agency Hamptons

  52 S Midway Rd, Shelter Island, NY 11964
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  /22

  $125,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  39 Congdon Rd, Shelter Island, NY 11964

  Lovely waterfront home with 3 bedrooms and 2.5 baths in the main house and a one bedrooms one bath guest cottage with kitchenette. Heated gunite swimming pool, dock, and private gardens. Available for rent for a yearly rental. Asking: $125K plus utilities and services.

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  39 Congdon Rd, Shelter Island, NY 11964
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  $2,500,000 Sold Feb 11, 2025

  18 Dickerson Dr, Shelter Island, NY 11786

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1973

  Last Sold Summary

  • $901/SF
  • 16 Days On Market

  Current Estimated Value $2,478,200

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate

  18 Dickerson Dr, Shelter Island, NY 11786
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  Est $799,935 Not Listed For Sale

  3 N Cartwright Rd, Shelter Island, NY 11964

  3 N Cartwright Rd, Shelter Island, NY 11964
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  $5,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,206 Sq Ft

  5 N Menantic Rd, Shelter Island, NY 11964

  A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living. In an iconic Shelter Island location on West

  Myles Reilly Saunders & Associates

  5 N Menantic Rd, Shelter Island, NY 11964
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  /20

  $40,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  37 Gardiners Bay Dr, Shelter Island, NY 11964

  Within close proximity to sandy Hay Beach, this immaculate 4 bedroom, 4 bath cedar shingled three-level modern has the spirit of living in a birds nest with sliding glass doors and porches everywhere overlooking cherry trees and wrap around deck, bay breezes blow throughout gently. The kitchen is a chef's delight, with granite counters, maple cabinets, Viking stove, Monogram refrigerator, Bosch

  37 Gardiners Bay Dr, Shelter Island, NY 11964
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  $4,950,000 Sold May 30, 2025

  104 S Ferry Rd, Shelter Island, NY 11964

  • 5 Beds
  • 5.5 Baths
  • 4,040 Sq Ft
  • Built 2023

  Last Sold Summary

  • $1,225/SF
  • 14 Days On Market

  Current Estimated Value $4,985,281

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  104 S Ferry Rd, Shelter Island, NY 11964
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  Est $632,000 Not Listed For Sale

  169 N Ferry Rd, Shelter Island, NY 11964

  169 N Ferry Rd, Shelter Island, NY 11964
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  /28

  $4,495,000

  • 6 Beds
  • 8 Baths
  • 5,622 Sq Ft

  100 S Ferry Rd, Shelter Island, NY 11964

  A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style

  Christine Beckwith Douglas Elliman Real Estate

  100 S Ferry Rd, Shelter Island, NY 11964
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  /35

  $75,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • House for Rent

  15 Montclair Ave, Shelter Island, NY 11964

  Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

  Margot Reutter Corcoran

  15 Montclair Ave, Shelter Island, NY 11964
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  $2,799,000 Sold Nov 14, 2025

  12 Terry Dr, Shelter Island, NY 11964

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft
  • Built 2015

  Last Sold Summary

  • $666/SF
  • 24 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  12 Terry Dr, Shelter Island, NY 11964
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  Est $1,771,000 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft

  3 Bevan Place, Shelter Island, NY 11964

  3 Bevan Place, Shelter Island, NY 11964

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